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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:00:15 UTC
Update Date2021-10-13 06:59:16 UTC
HMDB IDHMDB0036827
Secondary Accession Numbers
  • HMDB36827
Metabolite Identification
Common NameSclareol
DescriptionSclareol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Sclareol.
Structure
Data?1563862933
Synonyms
ValueSource
(13R)-Labd-14-ene-8,13-diolHMDB
Labd-14-ene-8,13-diolHMDB
Labd-14-ene-8alpha, 13beta-diolMeSH
Sclareol oxideMeSH
Chemical FormulaC20H36O2
Average Molecular Weight308.4986
Monoisotopic Molecular Weight308.271530396
IUPAC Name1-(3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
Traditional Namesclareol
CAS Registry Number515-03-7
SMILES
CC(O)(CCC1C(C)(O)CCC2C(C)(C)CCCC12C)C=C
InChI Identifier
InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3
InChI KeyXVULBTBTFGYVRC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Labdane diterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105.5 - 106 °CNot Available
Boiling Point218.00 to 220.00 °C. @ 19.00 mm HgThe Good Scents Company Information System
Water Solubility0.082 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.233 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP10(4.39) g/LALOGPS
logP10(4.34) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.98 m³·mol⁻¹ChemAxon
Polarizability37.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.74231661259
DarkChem[M-H]-172.72931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sclareol,1TMS,#1C=CC(C)(CCC1C(C)(O)CCC2C(C)(C)CCCC21C)O[Si](C)(C)C2425.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Sclareol,1TMS,#2C=CC(C)(O)CCC1C(C)(O[Si](C)(C)C)CCC2C(C)(C)CCCC21C2391.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Sclareol,2TMS,#1C=CC(C)(CCC1C(C)(O[Si](C)(C)C)CCC2C(C)(C)CCCC21C)O[Si](C)(C)C2401.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Sclareol,1TBDMS,#1C=CC(C)(CCC1C(C)(O)CCC2C(C)(C)CCCC21C)O[Si](C)(C)C(C)(C)C2679.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Sclareol,1TBDMS,#2C=CC(C)(O)CCC1C(C)(O[Si](C)(C)C(C)(C)C)CCC2C(C)(C)CCCC21C2626.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Sclareol,2TBDMS,#1C=CC(C)(CCC1C(C)(O[Si](C)(C)C(C)(C)C)CCC2C(C)(C)CCCC21C)O[Si](C)(C)C(C)(C)C2900.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sclareol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-3290000000-f9ddd13ff0c9310704c72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sclareol GC-MS (2 TMS) - 70eV, Positivesplash10-000i-6302900000-625e7a58372c1b4541a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sclareol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Positive-QTOFsplash10-052f-0092000000-2d33d9349017ace099c92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Positive-QTOFsplash10-0603-3190000000-de701adb29576c2596572015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Positive-QTOFsplash10-0kur-9870000000-4b30f5fc6d71b9a7f3412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Positive-QTOFsplash10-052f-0092000000-2d33d9349017ace099c92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Positive-QTOFsplash10-0603-3190000000-de701adb29576c2596572015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Positive-QTOFsplash10-0kur-9870000000-4b30f5fc6d71b9a7f3412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Negative-QTOFsplash10-0a4i-0049000000-f1667e5bf276e46930cd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Negative-QTOFsplash10-0a4r-0096000000-64ed7fe3eed1d6617ae32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Negative-QTOFsplash10-00kf-5090000000-5625e7493ab215e166882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Negative-QTOFsplash10-0a4i-0049000000-f1667e5bf276e46930cd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Negative-QTOFsplash10-0a4r-0096000000-64ed7fe3eed1d6617ae32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Negative-QTOFsplash10-00kf-5090000000-5625e7493ab215e166882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Positive-QTOFsplash10-0596-0091000000-0e4b22317072540f6eab2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Positive-QTOFsplash10-00dl-4690000000-8edc7a5b35b4f9e6dc482021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Positive-QTOFsplash10-014i-9210000000-b3d073d61468be9edcad2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 10V, Negative-QTOFsplash10-0a4i-0009000000-5728f2384b4de1f695b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 20V, Negative-QTOFsplash10-0a4r-0079000000-ce1dfba617eb8235fffc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sclareol 40V, Negative-QTOFsplash10-066u-9640000000-c2adcd7d19ed8a27a25a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015776
KNApSAcK IDC00000894
Chemspider ID454751
KEGG Compound IDC09183
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSclareol
METLIN IDNot Available
PubChem Compound521332
PDB IDNot Available
ChEBI ID9053
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hayet E, Fatma B, Souhir I, Waheb FA, Abderaouf K, Mahjoub A, Maha M: Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. Pak J Pharm Sci. 2007 Apr;20(2):146-8. [PubMed:17416571 ]
  2. Patel NR, Hatziantoniou S, Georgopoulos A, Demetzos C, Torchilin VP, Weissig V, D'Souza GG: Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol. J Liposome Res. 2010 Sep;20(3):244-9. doi: 10.3109/08982100903347931. [PubMed:19883213 ]
  3. van den Brule S, Muller A, Fleming AJ, Smart CC: The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol. Plant J. 2002 Jun;30(6):649-62. [PubMed:12061897 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.